Mild and general method for the α-Arylation of heteroaromatic ketones

Organic Letters

Volumn 12, Issue 5, 2010, Pages 1032-1035

  Desai, Lopa V ^a   Ren, Danan T ^a   Rosner, Thorsten ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; PH;

CATALYSIS; HYDROGEN-ION CONCENTRATION; KETONES; LIGANDS; PALLADIUM;

EID: 77749273809     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1000318     Document Type: Article

References (34)

1. (a) Hendrikson, J. B.; Bogard, T. L.; Fisch, M. E.; Grossert, S.; Yoshimura, N. J. Am. Chem. Soc. 1974, 96, 7781.
2. (b) Corey, E. J.; Guzman- Perez, A. Chem., Int. Ed. 1998, 37, 388.
3. (c) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147.
4. (d) Yokoshima, S.; Keda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137.
5. (a) Culkin, D. A.; Hartwig, J. F. Chem. Res. 2003, 36, 234.
6. (b) Bellina, F.; Rossi, R. Chem. Rev. 2009, DOI: 10.1021/cr9000836.
7. (a) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
8. (b) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 279, 211.
9. (c) Terao, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2002, 43, 101.
10. (d) Miura, M.; Satoh, T. Palladium in Organic Synthesis; Springer: Berlin/Heidelberg, 2005; Vol. 14.
11. (e) Terao, Y.; Fukuoka, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2002, 43, 101.
12. (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
13. (b) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.
14. (c) Moradi, W. A.; Buchwald, S. L. J. Am Chem. Soc. 2001, 123,7996.
15. (d) Martýn, R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 7236.
16. (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
17. (b) Hama, T.; Liu, X.; Culkin, D.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 11176.
18. (c) Liu, X.; Hartwig, J. F. J. Am Chem. Soc. 2004, 126, 5182.
19. (d) Vo, G. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2008, 47, 2127.
20. Biscoe, M. R.; Buchwald, S. L. Org. Lett. 2009, 11, 1773.
21. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881, and references therein.
22. °C. The monoarylated product is formed in. 57% yield, as a 2.5:1 mixture of mono and diarylated products.
23. (a) Yao, Z.; Zhou, H. Method for synthesis of Sinomenine derivative with C ring connected with pyrazine and its application in immunomoduIator. Faming Zhuanli Shenqing Gongkai Shuomingshu CN 1687065, October 26, 2005.
24. (b) Buhr, C. A.; Baik, T.-G.; Ma, S.; Tesfai, Z.; Wang, L.; Co, E. W.; Epshteyn, S.; Kennedy, A. R.; Chen, B.; Dubenko, L.; Anand, N. K.; Tsang, T. H.; Nuss, J. M.; Peto, C. J.; Rice, K. D.; Ibrahim, M. A.; Schnepp, K. L.; Shi, X.; Leahy, J. W.; Chen, J.; Dalrymple, L. E.; Forsyth, T. P.; Huynh, T. P.; Mann, G.; Mann, L. W.; Takeuchi, C. S. Preparation of substituted pyrazines as protein kinase modulators. WO 2003093297, November 13, 2003.
25. Refs 4 and 5 illustrate that excess ketone is generally used for α-arylation reactions.
26. 4 as base in. toluene at 100 °C. To the best of our knowledge, this is the first report of using cataCXiumPOMeCy as a ligand for an α-arylation reaction, making it a valuable alternative.
27. The effect of the position of the heteroatom. on reactivity in the context of Suzuki reactions has been, studied. Kondolff, I.; Doucet, H.; Santelli, M. J. Heterocycl, Chem. 2008, 45, 109.
28. Lugnier, C.; Dore, J. C.; Viel, C. Eur. J. Med. Chem. 1994, 29, 723.
29. (a) Barluenga, J.; Jimenez-Aquino, A.; Valdes, C.; Aznar, F. Angew; Chem. Int. Ed. 2007, 46, 1529.
30. (b) Barluenga, J.; Jimenez-Aquino, A.; Aznar, F.; Valdes, C. J. Am. Chem. Soc. 2009, 131, 4031.
31. Ref 5a discusses that the selectivity between mono- and diarylation is base-dependent. Arylations of electron-rich or electron-neutral aryl bromides were more selective for monoarylation with. KHMDS as the base, while electron-deficient aryl bromides were more selective with NaOtBU as the base.
32. Rosenthal, J.; Schuster, D. I. J. Chem. Educ. 2003, 80, 679.
33. (a) The effect of heteroaryl halides on reductive elimination in the context of amination chemistry has been studied. However, the impact of ligand to metal ratio was not explored. Hooper, M. W.; Hartwig, J. F. Organometallics 2003, 22, 3394-3403.
34. (b) Guram, A. S.; Wang, X.; Bunel, E. E.; Faul, M. M. Larsen, R. D.; Martinelli, M. J. Org. Chem. 2007, 72, 5104-5112.